Nucleophilic substitution on the ultimate hepatacarcinogen N-(sulfonatooxy)-2-(acetylamino)fluorene by aromatic amines

A unimolecular nucleophilic substitution (SN1) mechanism characterizes the reaction of N-(sulfonatooxy)-2-(acetylamino)fluorene with the aromatic amines, aniline and N,N-dimythelaniline. The observations on the kinetics and products of the reaction reveal the occurrence of an insubstantial overall rate effect and independent product yields. The study shows that the steric hindrance caused by the nitrogen in the fluorene compound apparently facilitates the alteration of the SN2 process leading to the development of the SN1 process.